Thionyl Chloride → 4-Chlorobenzenepropanol
Reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10](O)=[O:11])=[CH:4][CH:3]=1.S(Cl)(Cl)=O>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][CH2:10][OH:11])=[CH:6][CH:7]=1Participants
3
Procedure
After a mixture of 3-(4-chlorophenyl)propionic acid (5.00 g, 27.0 mmol) and thionyl chloride (3 ml) was refluxed for 2 hours, an excess of the thionyl chloride was distilled away under reduced pressure. The resultant residues were dissolved in tetrahydrofuran (200 ml), dropped slowly to a suspension of LiAlH4 in tetrahydrofuran at 0° C. and stirred at room temperature for 1 hour. Water and 1 N aqueous sodium hydroxide were added to the reaction mixture, and after insolubles were filtered off, the filtrate was dried over anhydrous magnesium sulfate. The solvent was distilled away under reduced pressure, whereby 4.6 g 3-(4-chlorophenyl)propyl alcohol was obtained as oily matter.
Workup
- temperaturewas refluxed for 2 hours
- distillationan excess of the thionyl chloride was distilled away under reduced pressure
- dissolutionThe resultant residues were dissolved in tetrahydrofuran (200 ml)
- additiondropped slowly to a suspension of LiAlH4 in tetrahydrofuran at 0° C.
- additionWater and 1 N aqueous sodium hydroxide were added to the reaction mixture
- filtrationafter insolubles were filtered off
- dry with materialthe filtrate was dried over anhydrous magnesium sulfate
- distillationThe solvent was distilled away under reduced pressure
Sources & evidence
- ORD record
- ord-a94f22fa71354572a402450aa89e7435
- Source dataset
- uspto-grants-2007_06
- Patent number
- US07229986B2
Reaction notes
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